ST 21:2;O3 (BioDeep_00000637522)

Main id: BioDeep_00000005729

Secondary id: BioDeep_00000005548, BioDeep_00000006137, BioDeep_00000012042, BioDeep_00000174007, BioDeep_00000405254, BioDeep_00000873120, BioDeep_00001869614, BioDeep_00001874342, BioDeep_00001901177

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


3beta,6alpha-dihydroxy-5alpha-pregn-9(11)-en-20-one

化学式: C21H32O3 (332.23513219999995)
中文名称: 17α-羟基孕烯醇酮, 4-孕烯-17α,20α-二醇-3-酮, 21-羟基孕烯醇酮, 5α-二氢脱氧皮质酮-d7, 17alpha-羟基孕烯醇酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.04%

分子结构信息

SMILES: C1CC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@](O)(C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]12C
InChI: InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h14,16-18,24H,4-12H2,1-3H3/t14-,16+,17-,18-,19-,20-,21-/m0/s1

描述信息

A hydroxypregnenolone that is pregnenolone substituted by a alpha-hydroxy group at position 16.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
17a-Hydroxypregnenolone is a pregnane steroid. 17a-Hydroxypregnenolone is a prohormone in the formation of dehydroepiandrosterone (DHEA).
21-Hydroxypregnenolone is an essential intermediate in corticosterone synthesis.

同义名列表

29 个代谢物同义名

(3beta,16alpha)-3,16-dihydroxypregn-5-en-20-one; 3beta,16alpha-dihydroxypregn-5-en-20-one; 5-Pregnen-3-beta,16-alpha-diol-20-one; 16-alpha-Hydroxypregnenolone; 16alpha-hydroxypregnenolone; ST 21:2;O3; 17alpha-hydroxy-5alpha-dihydroprogesterone; (5alpha)-17-Hydroxypregnane-3,20-dione; 5alpha-Pregnan-17alpha-ol-3,20-dione; 3beta,6alpha-dihydroxy-5alpha-pregn-9(11)-en-20-one; 17alpha,20alpha-Dihydroxypregn-4-en-3-one; (20S)-17,20-dihydroxypregn-4-en-3-one; 20-alfa-Dhydrodydrogesterone; Pregn-5-en-20-one,3,21-dihydroxy-, (3b)-; (3beta)-3,21-dihydroxypregn-5-en-20-one; 3beta,21-dihydroxypregn-5-en-20-one; 21-hydroxypregnenolone; 17,20-dihydroxypregn-4-en-3-one; 5A-PREGNAN-21-OL-3-20-DIONE CRYSTALLINE; 21-hydroxy-5alpha-pregnane-3,20-dione; 5alpha-dihydrodeoxycorticosterone; 3beta,17alpha-dihydroxypregn-5-en-20-one; Pregn-5-ene-3alpha,17alpha-diol-20-one; 17alpha-hydroxypregnenolone; 17a-Hydroxypregnenolone; 17alpha,20alpha-Dihydroxypregn-4-en-3-one; 16alpha-Hydroxypregnenolone; 17alpha-Hydroxypregnenolone; 21-Hydroxypregnenolone



数据库引用编号

60 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(1)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • V A Filatova, R V Rozhivanov, I Z Bondarenko, V A Ioutsi, E N Andreeva, G A Mel'nichenko, N G Mokrysheva. [Features of steroidogenesis and arterial hypertension in men in different types of "physiological" male hyperandrogenism]. Problemy endokrinologii. 2023 May; 69(2):80-91. doi: 10.14341/probl13226. [PMID: 37448275]
  • Johanna Ruhnau, Stephanie Hübner, Donna Sunny, Till Ittermann, Michaela F Hartmann, Jan De Lafollie, Stefan A Wudy, Matthias Heckmann. Impact of Gestational and Postmenstrual Age on Excretion of Fetal Zone Steroids in Preterm Infants Determined by Gas Chromatography-Mass Spectrometry. The Journal of clinical endocrinology and metabolism. 2021 08; 106(9):e3725-e3738. doi: 10.1210/clinem/dgab194. [PMID: 33822093]
  • Marco Mezzullo, Carla Pelusi, Alessia Fazzini, Andrea Repaci, Guido Di Dalmazi, Alessandra Gambineri, Uberto Pagotto, Flaminia Fanelli. Female and male serum reference intervals for challenging sex and precursor steroids by liquid chromatography - tandem mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2020 03; 197(?):105538. doi: 10.1016/j.jsbmb.2019.105538. [PMID: 31734493]
  • Abdelmoneim Khashana, Hoda Ahmed, Amal Ahmed, Amina Abdelwahab, Timo Saarela, Mika Rämet, Mikko Hallman. Cortisol precursors in neonates with vasopressor-resistant hypotension in relationship to demographic characteristics. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians. 2018 Sep; 31(18):2473-2477. doi: 10.1080/14767058.2017.1344966. [PMID: 28629239]
  • Christopher M Jones, Ashwini Mallappa, Nicole Reisch, Nikolaos Nikolaou, Nils Krone, Beverly A Hughes, Donna M O'Neil, Martin J Whitaker, Jeremy W Tomlinson, Karl-Heinz Storbeck, Deborah P Merke, Richard J Ross, Wiebke Arlt. Modified-Release and Conventional Glucocorticoids and Diurnal Androgen Excretion in Congenital Adrenal Hyperplasia. The Journal of clinical endocrinology and metabolism. 2017 06; 102(6):1797-1806. doi: 10.1210/jc.2016-2855. [PMID: 27845856]
  • Patrizia Porcu, Todd K O'Buckley, Marcelo F Lopez, Howard C Becker, Michael F Miles, Robert W Williams, A Leslie Morrow. Initial genetic dissection of serum neuroactive steroids following chronic intermittent ethanol across BXD mouse strains. Alcohol (Fayetteville, N.Y.). 2017 Feb; 58(?):107-125. doi: 10.1016/j.alcohol.2016.07.011. [PMID: 27884493]
  • Changzhuan Shao, Yiming Ren, Zinan Wang, Chenzhe Kang, Hongke Jiang, Aiping Chi. Detection of Urine Metabolites in a Rat Model of Chronic Fatigue Syndrome before and after Exercise. BioMed research international. 2017; 2017(?):8182020. doi: 10.1155/2017/8182020. [PMID: 28421200]
  • Shin-Hye Kim, Ju-Yeon Moon, Hironobu Sasano, Man Ho Choi, Mi-Jung Park. Body Fat Mass Is Associated With Ratio of Steroid Metabolites Reflecting 17,20-Lyase Activity in Prepubertal Girls. The Journal of clinical endocrinology and metabolism. 2016 12; 101(12):4653-4660. doi: 10.1210/jc.2016-2515. [PMID: 27648966]
  • Juilee Rege, Shigehiro Karashima, Antonio M Lerario, Joshua M Smith, Richard J Auchus, Josephine Z Kasa-Vubu, Hironobu Sasano, Yasuhiro Nakamura, Perrin C White, William E Rainey. Age-dependent Increases in Adrenal Cytochrome b5 and Serum 5-Androstenediol-3-sulfate. The Journal of clinical endocrinology and metabolism. 2016 12; 101(12):4585-4593. doi: 10.1210/jc.2016-2864. [PMID: 27623070]
  • Antonín Pařízek, Martin Hill, Michaela Dušková, Libor Vítek, Marta Velíková, Radmila Kancheva, Patrik Šimják, Michal Koucký, Zuzana Kokrdová, Karolína Adamcová, Andrej Černý, Zdeněk Hájek, Luboslav Stárka. A Comprehensive Evaluation of Steroid Metabolism in Women with Intrahepatic Cholestasis of Pregnancy. PloS one. 2016; 11(8):e0159203. doi: 10.1371/journal.pone.0159203. [PMID: 27494119]
  • Yuanxiang Jin, Xiaojian Lin, Wenyu Miao, Linggang Wang, Yan Wu, Zhengwei Fu. Oral exposure of pubertal male mice to endocrine-disrupting chemicals alters fat metabolism in adult livers. Environmental toxicology. 2015 Dec; 30(12):1434-44. doi: 10.1002/tox.22013. [PMID: 24916741]
  • Ariadni Spyroglou, Anna Riester, Katharina Mueller-Peltzer, Ailing Lu, Juliane Rohde, Constanze Hantel, Claudia Kuehne, Alexandra Kulle, Felix Riepe, Jan M Deussing, Felix Beuschlein. Adrenal and Ovarian Phenotype of a Tissue-Specific Urocortin 2-Overexpressing Mouse Model. Endocrinology. 2015 Jul; 156(7):2646-56. doi: 10.1210/en.2014-1971. [PMID: 25942073]
  • Vitor Guilherme Brito de Araújo, Renata Santarem de Oliveira, Kallianna Paula Duarte Gameleira, Cátia Barbosa Cruz, Adriana Lofrano-Porto. 3β-hydroxysteroid dehydrogenase type II deficiency on newborn screening test. Arquivos brasileiros de endocrinologia e metabologia. 2014 Aug; 58(6):650-5. doi: 10.1590/0004-2730000003098. [PMID: 25211449]
  • Na Na Kim, Hyun Suk Shin, Young Jae Choi, Cheol Young Choi. Kisspeptin regulates the hypothalamus-pituitary-gonad axis gene expression during sexual maturation in the cinnamon clownfish, Amphiprion melanopus. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2014 Feb; 168(?):19-32. doi: 10.1016/j.cbpb.2013.11.002. [PMID: 24239680]
  • Hyun Suk Shin, Hamid R Habibi, Cheol Young Choi. The environmental regulation of maturation in goldfish, Carassius auratus: effects of various LED light spectra. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2014 Feb; 168(?):17-24. doi: 10.1016/j.cbpa.2013.11.003. [PMID: 24239668]
  • D Kariyawasam, A Simon, K Laborde, S Parat, P-F Souchon, P Frange, S Blanche, M Polak. Adrenal enzyme impairment in neonates and adolescents treated with ritonavir and protease inhibitors for HIV exposure or infection. Hormone research in paediatrics. 2014; 81(4):226-31. doi: 10.1159/000356916. [PMID: 24577112]
  • Amir Kalani, Gul Bahtiyar, Alan Sacerdote. Ashwagandha root in the treatment of non-classical adrenal hyperplasia. BMJ case reports. 2012 Sep; 2012(?):. doi: 10.1136/bcr-2012-006989. [PMID: 22987912]
  • Shogo Haraguchi, Teppei Koyama, Itaru Hasunuma, Shin-ichiro Okuyama, Takayoshi Ubuka, Sakae Kikuyama, Jean-Luc Do Rego, Hubert Vaudry, Kazuyoshi Tsutsui. Acute stress increases the synthesis of 7α-hydroxypregnenolone, a new key neurosteroid stimulating locomotor activity, through corticosterone action in newts. Endocrinology. 2012 Feb; 153(2):794-805. doi: 10.1210/en.2011-1422. [PMID: 22128027]
  • Ian A E Butts, Oliver P Love, Michelle Farwell, Trevor E Pitcher. Primary and secondary sexual characters in alternative reproductive tactics of Chinook salmon: Associations with androgens and the maturation-inducing steroid. General and comparative endocrinology. 2012 Feb; 175(3):449-56. doi: 10.1016/j.ygcen.2011.11.041. [PMID: 22172341]
  • Martin Hill, Jana Vrbíková, Jana Zárubová, Radmila Kancheva, Marta Velíková, Lyudmila Kancheva, Jana Kubátová, Michaela Dušková, Petr Marusič, Antonín Pařízek, Luboslav Stárka. The steroid metabolome in lamotrigine-treated women with epilepsy. Steroids. 2011 Nov; 76(12):1351-7. doi: 10.1016/j.steroids.2011.07.002. [PMID: 21787799]
  • Efthimia Antonopoulou, Athanassios C Tsikliras, Martin Kocour, Vladimir Zlábek, Martin Flajšhans, David Gela, Veronika Piačková, Alexander P Scott. Teleost maturation-inducing hormone, 17,20β-dihydroxypregn-4-en-3-one, peaks after spawning in Tinca tinca. General and comparative endocrinology. 2011 Jun; 172(2):234-42. doi: 10.1016/j.ygcen.2011.03.008. [PMID: 21420410]
  • Yogesh Kumar Katare, Alexander P Scott, Alyson J Laframboise, Weiming Li, Zena Alyasha'e, Christopher B Caputo, Stephen J Loeb, Barbara Zielinski. Release of free and conjugated forms of the putative pheromonal steroid 11-oxo-etiocholanolone by reproductively mature male round goby (Neogobius melanostomus Pallas, 1814). Biology of reproduction. 2011 Feb; 84(2):288-98. doi: 10.1095/biolreprod.110.086546. [PMID: 20944082]
  • Ryuji Kouyama, Kiichiro Hiraishi, Toru Sugiyama, Hajime Izumiyama, Takanobu Yoshimoto, Takumi Akashi, Kazunori Kihara, Keiko Homma, Hirotaka Shibata, Yukio Hirata. Clinicopathological features, biochemical and molecular markers in 5 patients with adrenocortical carcinoma. Endocrine journal. 2011; 58(7):527-34. doi: 10.1507/endocrj.k11e-026. [PMID: 21521927]
  • E Cabrita, F Soares, J Beirão, A García-López, G Martínez-Rodríguez, M T Dinis. Endocrine and milt response of Senegalese sole, Solea senegalensis, males maintained in captivity. Theriogenology. 2011 Jan; 75(1):1-9. doi: 10.1016/j.theriogenology.2010.07.003. [PMID: 20833416]
  • Liliya Bykova, Stephanie A Archer-Hartmann, Lisa A Holland, Luke R Iwanowicz, Vicki S Blazer. Steroid determination in fish plasma using capillary electrophoresis. Environmental toxicology and chemistry. 2010 Sep; 29(9):1950-6. doi: 10.1002/etc.252. [PMID: 20821652]
  • H Tveiten, M Frantzen, A M Scott, A P Scott. Synthesis of 17,20beta,21-trihydroxypregn-4-en-3-one by ovaries of reproductively mature Atlantic cod Gadus morhua. Journal of fish biology. 2010 Jul; 77(1):33-53. doi: 10.1111/j.1095-8649.2010.02655.x. [PMID: 20646137]
  • David S Peñaranda, Luz Pérez, Víctor Gallego, Miguel Jover, Helge Tveiten, Sylvie Baloche, Sylvie Dufour, Juan F Asturiano. Molecular and physiological study of the artificial maturation process in European eel males: from brain to testis. General and comparative endocrinology. 2010 Mar; 166(1):160-71. doi: 10.1016/j.ygcen.2009.08.006. [PMID: 19699741]
  • A P Scott, J P Sumpter, N Stacey. The role of the maturation-inducing steroid, 17,20beta-dihydroxypregn-4-en-3-one, in male fishes: a review. Journal of fish biology. 2010 Jan; 76(1):183-224. doi: 10.1111/j.1095-8649.2009.02483.x. [PMID: 20738705]
  • Sungchang Choi, Cheul Ho Lee, Woodong Park, Dae-Jung Kim, Young Chang Sohn. Effects of shortened photoperiod on gonadotropin-releasing hormone, gonadotropin, and vitellogenin gene expression associated with ovarian maturation in rainbow trout. Zoological science. 2010 Jan; 27(1):24-32. doi: 10.2108/zsj.27.24. [PMID: 20064005]
  • Terence P Barry, Ashok Marwah, Scott Nunez. Inhibition of cortisol metabolism by 17alpha,20beta-P: mechanism mediating semelparity in salmon?. General and comparative endocrinology. 2010 Jan; 165(1):53-9. doi: 10.1016/j.ygcen.2009.06.003. [PMID: 19523470]
  • Päivi Nykänen, Kirsti Heinonen, Felix G Riepe, Wolfgang G Sippell, Raimo Voutilainen. Serum concentrations of adrenal steroids and their precursors as a measure of maturity of adrenocortical function in very premature newborns. Hormone research in paediatrics. 2010; 74(5):358-64. doi: 10.1159/000314970. [PMID: 20606393]
  • Marie-Claude Villeneuve, Richard E Ostlund, Jean-Patrice Baillargeon. Hyperinsulinemia is closely related to low urinary clearance of D-chiro-inositol in men with a wide range of insulin sensitivity. Metabolism: clinical and experimental. 2009 Jan; 58(1):62-8. doi: 10.1016/j.metabol.2008.08.007. [PMID: 19059532]
  • Yu-Wen Chung-Davidson, Christopher Benjamin Rees, Mara Beth Bryan, Weiming Li. Neurogenic and neuroendocrine effects of goldfish pheromones. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2008 Dec; 28(53):14492-9. doi: 10.1523/jneurosci.3589-08.2008. [PMID: 19118184]
  • Ky Xuan Pham, Masafumi Amano, Yutaka Kurita, Akio Shimizu, Yuichiro Fujinami, Noriko Amiya, Kunio Yamamori. Changes in the immunostaining intensities of follicle-stimulating hormone and luteinizing hormone during ovarian maturation in the female Japanese flounder. Fish physiology and biochemistry. 2008 Dec; 34(4):357-65. doi: 10.1007/s10695-007-9195-9. [PMID: 18958593]
  • Erik Vikingstad, Eva Andersson, Birgitta Norberg, Ian Mayer, Ulrike Klenke, Yonathan Zohar, Sigurd Olav Stefansson, Geir Lasse Taranger. The combined effects of temperature and GnRHa treatment on the final stages of sexual maturation in Atlantic salmon (Salmo salar L.) females. Fish physiology and biochemistry. 2008 Sep; 34(3):289-98. doi: 10.1007/s10695-007-9187-9. [PMID: 18665466]
  • Sylvain Milla, Xavier Terrien, Armin Sturm, Fidaa Ibrahim, Franck Giton, Jean Fiet, Patrick Prunet, Florence Le Gac. Plasma 11-deoxycorticosterone (DOC) and mineralocorticoid receptor testicular expression during rainbow trout Oncorhynchus mykiss spermiation: implication with 17alpha, 20beta-dihydroxyprogesterone on the milt fluidity?. Reproductive biology and endocrinology : RB&E. 2008 May; 6(?):19. doi: 10.1186/1477-7827-6-19. [PMID: 18489781]
  • Eric S Clelland, Qian Tan, Ari Balofsky, Rosie Lacivita, Chun Peng. Inhibition of premature oocyte maturation: a role for bone morphogenetic protein 15 in zebrafish ovarian follicles. Endocrinology. 2007 Nov; 148(11):5451-8. doi: 10.1210/en.2007-0674. [PMID: 17656459]
  • P B Singh, Vandana Singh, Shailly Srivastava, S Pandey. Effects of estradiol-17beta and 17alpha, 20beta-dihydroxy-4-pregnen-3-one on different phospholipids metabolism and histological changes in ovary during reproductive growth in the catfish, Heteropneustes fossilis (Bloch). Journal of environmental biology. 2007 Oct; 28(4):771-8. doi: NULL. [PMID: 18405111]
  • Maria J Agulleiro, Alexander P Scott, Neil Duncan, Constantinos C Mylonas, Joan Cerdà. Treatment of GnRHa-implanted Senegalese sole (Solea senegalensis) with 11-ketoandrostenedione stimulates spermatogenesis and increases sperm motility. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2007 Aug; 147(4):885-92. doi: 10.1016/j.cbpa.2007.02.008. [PMID: 17360211]
  • Helena Vceláková, Martin Hill, Oldrich Lapcík, Antonín Parízek. Determination of 17alpha-hydroxypregnenolone sulfate and its application in diagnostics. Steroids. 2007 Apr; 72(4):323-7. doi: 10.1016/j.steroids.2006.11.026. [PMID: 17298837]
  • Angel García-López, Elsa Couto, Adelino V M Canario, Carmen Sarasquete, Gonzalo Martínez-Rodríguez. Ovarian development and plasma sex steroid levels in cultured female Senegalese sole Solea senegalensis. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2007 Mar; 146(3):342-54. doi: 10.1016/j.cbpa.2006.11.014. [PMID: 17208478]
  • Alia Jaensson, Alexander P Scott, Andrew Moore, Henrik Kylin, K Håkan Olsén. Effects of a pyrethroid pesticide on endocrine responses to female odours and reproductive behaviour in male parr of brown trout (Salmo trutta L.). Aquatic toxicology (Amsterdam, Netherlands). 2007 Feb; 81(1):1-9. doi: 10.1016/j.aquatox.2006.10.011. [PMID: 17174415]
  • K H Olsén, G R Sawisky, N E Stacey. Endocrine and milt responses of male crucian carp (Carassius carassius L.) to periovulatory females under field conditions. General and comparative endocrinology. 2006 Dec; 149(3):294-302. doi: 10.1016/j.ygcen.2006.06.011. [PMID: 16934255]
  • H Budzinski, M H Devier, P Labadie, A Togola. Analysis of hormonal steroids in fish plasma and bile by coupling solid-phase extraction to GC/MS. Analytical and bioanalytical chemistry. 2006 Nov; 386(5):1429-39. doi: 10.1007/s00216-006-0686-9. [PMID: 16906384]
  • Gail F Jurgella, Ashok Marwah, Jeffrey A Malison, Richard Peterson, Terence P Barry. Effects of xenobiotics and steroids on renal and hepatic estrogen metabolism in lake trout. General and comparative endocrinology. 2006 Sep; 148(2):273-81. doi: 10.1016/j.ygcen.2006.03.011. [PMID: 16677648]
  • Simon MacKenzie, Nuria Montserrat, Mario Mas, Laura Acerete, Lluis Tort, Aleksei Krasnov, Frederick W Goetz, Josep V Planas. Bacterial lipopolysaccharide induces apoptosis in the trout ovary. Reproductive biology and endocrinology : RB&E. 2006 Aug; 4(?):46. doi: 10.1186/1477-7827-4-46. [PMID: 16945135]
  • Mark M Kushnir, Alan L Rockwood, William L Roberts, Elizabeth G Pattison, William E Owen, Ashley M Bunker, A Wayne Meikle. Development and performance evaluation of a tandem mass spectrometry assay for 4 adrenal steroids. Clinical chemistry. 2006 Aug; 52(8):1559-67. doi: 10.1373/clinchem.2006.068445. [PMID: 16777916]
  • N S Sieber-Ruckstuhl, F S Boretti, M Wenger, C Maser-Gluth, C E Reusch. Cortisol, aldosterone, cortisol precursor, androgen and endogenous ACTH concentrations in dogs with pituitary-dependant hyperadrenocorticism treated with trilostane. Domestic animal endocrinology. 2006 Jul; 31(1):63-75. doi: 10.1016/j.domaniend.2005.09.004. [PMID: 16233969]
  • Jonghan Kim, William L Hayton, Irvin R Schultz. Modeling the brain-pituitary-gonad axis in salmon. Marine environmental research. 2006 Jul; 62 Suppl(?):S426-32. doi: 10.1016/j.marenvres.2006.04.022. [PMID: 16716390]
  • A García-López, V Fernández-Pasquier, E Couto, A V M Canario, C Sarasquete, G Martínez-Rodríguez. Testicular development and plasma sex steroid levels in cultured male Senegalese sole Solea senegalensis Kaup. General and comparative endocrinology. 2006 Jul; 147(3):343-51. doi: 10.1016/j.ygcen.2006.02.003. [PMID: 16574114]
  • Mar Huertas, Alexander P Scott, Peter C Hubbard, Adelino V M Canário, Joan Cerdà. Sexually mature European eels (Anguilla anguilla L.) stimulate gonadal development of neighbouring males: possible involvement of chemical communication. General and comparative endocrinology. 2006 Jul; 147(3):304-13. doi: 10.1016/j.ygcen.2006.01.017. [PMID: 16545383]
  • M Kusakabe, I Nakamura, J Evans, P Swanson, G Young. Changes in mRNAs encoding steroidogenic acute regulatory protein, steroidogenic enzymes and receptors for gonadotropins during spermatogenesis in rainbow trout testes. The Journal of endocrinology. 2006 Jun; 189(3):541-54. doi: 10.1677/joe.1.06684. [PMID: 16731785]
  • Barzan Bahrami Kamangar, Jean-Charles Gabillard, Julien Bobe. Insulin-like growth factor-binding protein (IGFBP)-1, -2, -3, -4, -5, and -6 and IGFBP-related protein 1 during rainbow trout postvitellogenesis and oocyte maturation: molecular characterization, expression profiles, and hormonal regulation. Endocrinology. 2006 May; 147(5):2399-410. doi: 10.1210/en.2005-1570. [PMID: 16439447]
  • Noriko Tagawa, Masanao Katagiri, Yoshiharu Kobayashi. Developmental changes of serum steroids produced by cytochrome P450c17 in rat. Steroids. 2006 Feb; 71(2):165-70. doi: 10.1016/j.steroids.2005.09.006. [PMID: 16280146]
  • Ikumi Nakamura, Jennifer C Evans, Makoto Kusakabe, Yoshitaka Nagahama, Graham Young. Changes in steroidogenic enzyme and steroidogenic acute regulatory protein messenger RNAs in ovarian follicles during ovarian development of rainbow trout (Oncorhynchus mykiss). General and comparative endocrinology. 2005 Dec; 144(3):224-31. doi: 10.1016/j.ygcen.2005.06.004. [PMID: 16102755]
  • Rainer H Straub, Peter Härle, Martin Kriegel, Jürgen Schölmerich, Hanns-Martin Lorenz. Adrenal and gonadal hormone variations during a febrile attack in a woman with tumor necrosis factor receptor-associated periodic syndrome. The Journal of clinical endocrinology and metabolism. 2005 Oct; 90(10):5884-7. doi: 10.1210/jc.2005-1016. [PMID: 16030167]
  • Livia M Mermejo, Lucila L K Elias, S Marui, Ayrton C Moreira, Berenice B Mendonca, Margaret de Castro. Refining hormonal diagnosis of type II 3beta-hydroxysteroid dehydrogenase deficiency in patients with premature pubarche and hirsutism based on HSD3B2 genotyping. The Journal of clinical endocrinology and metabolism. 2005 Mar; 90(3):1287-93. doi: 10.1210/jc.2004-1552. [PMID: 15585552]
  • Ken D Oakes, L Mark Hewitt, Mark E McMaster, Craig Wood, Kelly R Munkittrick, Glen J Van Der Kraak. Oxidative stress and sex steroid levels in fish following short-term exposure to pulp-mill effluents. Journal of toxicology and environmental health. Part A. 2005 Feb; 68(4):267-86. doi: 10.1080/15287390590895621. [PMID: 15799451]
  • Wen-Shiun Yueh, Peter Thomas, Ching-Fong Chang. Identification of 17,20beta,21-trihydroxy-4-pregnen-3-one as an oocyte maturation-inducing steroid in black porgy, Acanthopagrus schlegeli. General and comparative endocrinology. 2005 Feb; 140(3):184-91. doi: 10.1016/j.ygcen.2004.10.014. [PMID: 15639146]
  • P W Sorensen, C A Murphy, K Loomis, P Maniak, P Thomas. Evidence that 4-pregnen-17,20beta,21-triol-3-one functions as a maturation-inducing hormone and pheromonal precursor in the percid fish, Gymnocephalus cernuus. General and comparative endocrinology. 2004 Oct; 139(1):1-11. doi: 10.1016/j.ygcen.2004.05.014. [PMID: 15474530]
  • Daisuke Saito, Qiong Shi, Hironori Ando, Akihisa Urano. Attenuation of diurnal rhythms in plasma levels of melatonin and cortisol, and hypothalamic contents of vasotocin and isotocin mRNAs in pre-spawning chum salmon. General and comparative endocrinology. 2004 May; 137(1):62-8. doi: 10.1016/j.ygcen.2004.02.010. [PMID: 15094336]
  • Marie Bicíková, Daniela Rípová, Martin Hill, Roman Jirák, Helena Havlíková, Jaroslava Tallová, Richard Hampl. Plasma levels of 7-hydroxylated dehydroepiandrosterone (DHEA) metabolites and selected amino-thiols as discriminatory tools of Alzheimer's disease and vascular dementia. Clinical chemistry and laboratory medicine. 2004 May; 42(5):518-24. doi: 10.1515/cclm.2004.088. [PMID: 15202788]
  • Yasunori Koya, Hisanari Mori, Masahiro Nakagawa. Serum 17,20 beta-dihydroxy-4-pregnen-3-one Levels in pregnant and non-pregnant female rockfish, Sebastes schlegeli, viviparous teleost, and its production by post-ovulatory follicles. Zoological science. 2004 May; 21(5):565-73. doi: 10.2108/zsj.21.565. [PMID: 15170060]
  • Albert F H Ros, Adelino V M Canario, Elsa Couto, Iija Zeilstra, Rui F Oliveira. Endocrine correlates of intra-specific variation in the mating system of the St. Peter's fish (Sarotherodon galilaeus). Hormones and behavior. 2003 Nov; 44(4):365-73. doi: 10.1016/s0018-506x(03)00158-2. [PMID: 14613731]
  • Takeshi Onuma, Yoshitatsu Higashi, Hironori Ando, Masatoshi Ban, Hiroshi Ueda, Akihisa Urano. Year-to-year differences in plasma levels of steroid hormones in pre-spawning chum salmon. General and comparative endocrinology. 2003 Sep; 133(2):199-215. doi: 10.1016/s0016-6480(03)00171-0. [PMID: 12928010]
  • Diane Thiboutot, Sami Jabara, Jan M McAllister, Aruntha Sivarajah, Kathyrn Gilliland, Zhaoyuan Cong, Gary Clawson. Human skin is a steroidogenic tissue: steroidogenic enzymes and cofactors are expressed in epidermis, normal sebocytes, and an immortalized sebocyte cell line (SEB-1). The Journal of investigative dermatology. 2003 Jun; 120(6):905-14. doi: 10.1046/j.1523-1747.2003.12244.x. [PMID: 12787114]
  • Teresa Modesto, Adelino V M Canário. Morphometric changes and sex steroid levels during the annual reproductive cycle of the Lusitanian toadfish, Halobatrachus didactylus. General and comparative endocrinology. 2003 May; 131(3):220-31. doi: 10.1016/s0016-6480(03)00027-3. [PMID: 12714003]
  • Md Saydur Rahman, Masaya Morita, Akihiro Takemura, Kazunori Takano. Hormonal changes in relation to lunar periodicity in the testis of the forktail rabbitfish, Siganus argenteus. General and comparative endocrinology. 2003 May; 131(3):302-9. doi: 10.1016/s0016-6480(03)00025-x. [PMID: 12714013]
  • Daniela Vogl, Werner Falk, Monika Dorner, Jürgen Schölmerich, Rainer H Straub. Serum levels of pregnenolone and 17-hydroxypregnenolone in patients with rheumatoid arthritis and systemic lupus erythematosus: relation to other adrenal hormones. The Journal of rheumatology. 2003 Feb; 30(2):269-75. doi: . [PMID: 12563679]
  • Noriko Tagawa, Mitsuhiro Ohta, Naoto Nakamura, Koji Nakano, Hiroshi Obayashi, Yoshiharu Kobayashi. Serum concentrations of delta 5-3 beta-hydroxysteroids in type 2 diabetes mellitus. Biological & pharmaceutical bulletin. 2002 Dec; 25(12):1634-8. doi: 10.1248/bpb.25.1634. [PMID: 12499654]
  • P C Hubbard, E N Barata, A V M Canario. Possible disruption of pheromonal communication by humic acid in the goldfish, Carassius auratus. Aquatic toxicology (Amsterdam, Netherlands). 2002 Oct; 60(3-4):169-83. doi: 10.1016/s0166-445x(02)00002-4. [PMID: 12200084]
  • Molly A H Webb, Grant W Feist, John M Trant, Joel P Van Eenennaam, Martin S Fitzpatrick, Carl B Schreck, Serge I Doroshov. Ovarian steroidogenesis in white sturgeon (Acipenser transmontanus) during oocyte maturation and induced ovulation. General and comparative endocrinology. 2002 Oct; 129(1):27-38. doi: 10.1016/s0016-6480(02)00508-7. [PMID: 12409093]
  • Felix G Riepe, Philip Mahler, Wolfgang G Sippell, Carl-Joachim Partsch. Longitudinal study of plasma pregnenolone and 17-hydroxypregnenolone in full-term and preterm neonates at birth and during the early neonatal period. The Journal of clinical endocrinology and metabolism. 2002 Sep; 87(9):4301-6. doi: 10.1210/jc.2002-020452. [PMID: 12213889]
  • Stefan A Wudy, Michaela Hartmann, Janos Homoki. Determination of 11-deoxycortisol (Reichstein's compound S) in human plasma by clinical isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection. Steroids. 2002 Sep; 67(10):851-7. doi: 10.1016/s0039-128x(02)00052-1. [PMID: 12231120]
  • Hideaki Yamada, Ri-ichi Satoh, Masashi Ogoh, Keigo Takaji, Yasufumi Fujimoto, Takeshi Hakuba, Hiroaki Chiba, Akira Kambegawa, Munehico Iwata. Circadian changes in serum concentrations of steroids in Japanese char Salvelinus leucomaenis at the stage of final maturation. Zoological science. 2002 Aug; 19(8):891-8. doi: 10.2108/zsj.19.891. [PMID: 12193805]
  • M Rahman, Kohei Ohta, Michiyasu Yoshikuni, Yoshitaka Nagahama, Hisashi Chuda, Michiya Matsuyama. Characterization of ovarian membrane receptor for 17,20beta-dihydroxy-4-pregnen-3-one, a maturation-inducing hormone in yellowtail, Seriola quinqueradiata. General and comparative endocrinology. 2002 Jun; 127(1):71-9. doi: 10.1016/s0016-6480(02)00026-6. [PMID: 12161204]
  • J Vrbíková, M Bicíková, J Tallová, M Hill, L Stárka. Homocysteine and steroids levels in metformin treated women with polycystic ovary syndrome. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2002 Apr; 110(2):74-6. doi: 10.1055/s-2002-23489. [PMID: 11928069]
  • F G Riepe, S Wonka, C J Partsch, W G Sippell. Automated chromatographic system for the simultaneous measurement of plasma pregnenolone and 17-hydroxypregnenolone by radioimmunoassay. Journal of chromatography. B, Biomedical sciences and applications. 2001 Nov; 763(1-2):99-106. doi: 10.1016/s0378-4347(01)00373-5. [PMID: 11710589]
  • K H Olsén, R Bjerselius, I Mayer, H Kindahl. Both ovarian fluid and female urine increase sex steroid hormone levels in mature Atlantic salmon (Salmo salar) male parr. Journal of chemical ecology. 2001 Nov; 27(11):2337-49. doi: 10.1023/a:1012243323670. [PMID: 11817085]
  • S A Wudy, M Hartmann, C Solleder, J Homoki. Determination of 17alpha-hydroxypregnenolone in human plasma by routine isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection. Steroids. 2001 Oct; 66(10):759-62. doi: 10.1016/s0039-128x(01)00109-x. [PMID: 11522338]
  • A D Genazzani, C Bersi, S Luisi, F Fruzzetti, B Malavasi, M Luisi, F Petraglia, A R Genazzani. Increased adrenal steroid secretion in response to CRF in women with hypothalamic amenorrhea. The Journal of steroid biochemistry and molecular biology. 2001 Sep; 78(3):247-52. doi: 10.1016/s0960-0760(01)00094-2. [PMID: 11595505]
  • M R Palmert, D L Hayden, M J Mansfield, J F Crigler, W F Crowley, D W Chandler, P A Boepple. The longitudinal study of adrenal maturation during gonadal suppression: evidence that adrenarche is a gradual process. The Journal of clinical endocrinology and metabolism. 2001 Sep; 86(9):4536-42. doi: 10.1210/jcem.86.9.7863. [PMID: 11549704]
  • L N Greenwood, A P Scott, E L Vermeirssen, C C Mylonas, M Pavlidis. Plasma steroids in mature common dentex (Dentex dentex) stimulated with a gonadotropin-releasing hormone agonist. General and comparative endocrinology. 2001 Jul; 123(1):1-12. doi: 10.1006/gcen.2000.7519. [PMID: 11551110]
  • A Munakata, M Amano, K Ikuta, S Kitamura, K Aida. The involvement of sex steroid hormones in downstream and upstream migratory behavior of masu salmon. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2001 Jun; 129(2-3):661-9. doi: 10.1016/s1096-4959(01)00365-7. [PMID: 11399503]
  • M S Rahman, A Takemura, K Takano. Lunar synchronization of testicular development and steroidogenesis in rabbitfish. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2001 Jun; 129(2-3):367-73. doi: 10.1016/s1096-4959(01)00323-2. [PMID: 11399470]
  • A Moore, N Lower. The impact of two pesticides on olfactory-mediated endocrine function in mature male Atlantic salmon (Salmo salar L.) parr. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2001 Jun; 129(2-3):269-76. doi: 10.1016/s1096-4959(01)00321-9. [PMID: 11399459]
  • J Rinchard, K Dabrowski, J Ottobre. Sex steroids in plasma of lake whitefish Coregonus clupeaformis during spawning in Lake Erie. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2001 May; 129(1):65-74. doi: 10.1016/s1095-6433(01)00353-1. [PMID: 11369302]
  • A Moore, C P Waring. The effects of a synthetic pyrethroid pesticide on some aspects of reproduction in Atlantic salmon (Salmo salar L.). Aquatic toxicology (Amsterdam, Netherlands). 2001 Mar; 52(1):1-12. doi: 10.1016/s0166-445x(00)00133-8. [PMID: 11163426]
  • L J Barcellos, G F Wassermann, A P Scott, V M Woehl, R M Quevedo, I Ittzés, M H Krieger, F Lulhier. Steroid profiles in cultured female jundiá, the Siluridae Rhamdia quelen (Quoy and Gaimard, Pisces Teleostei), during the first reproductive cycle. General and comparative endocrinology. 2001 Mar; 121(3):325-32. doi: 10.1006/gcen.2001.7603. [PMID: 11254374]
  • J Fiet, F Giton, A Boudi, P Boudou, H Soliman, J Villette, H Galons. Plasma 17-OH pregnenolone: comparison of a time-resolved fluoroimmunoassay using a new tracer 17-OH pregnenolone-3-oxyacetyl-biotine with a radioimmunoassay using 125I 17-OH pregnenolone-3-hemisuccinate-histamine. Steroids. 2001 Feb; 66(2):81-6. doi: 10.1016/s0039-128x(00)00207-5. [PMID: 11146086]
  • M Bicíková, J Tallová, M Hill, Z Krausová, R Hampl. Serum concentrations of some neuroactive steroids in women suffering from mixed anxiety-depressive disorder. Neurochemical research. 2000 Dec; 25(12):1623-7. doi: 10.1023/a:1026622704704. [PMID: 11152391]
  • R Huerta, D Dewailly, C Decanter, E S Knochenhauer, L R Boots, R Azziz. Adrenocortical hyperresponsivity to adrenocorticotropic hormone: a mechanism favoring the normal production of cortisol in 21-hydroxylase-deficient nonclassic adrenal hyperplasia. Fertility and sterility. 2000 Aug; 74(2):329-34. doi: 10.1016/s0015-0282(00)00631-2. [PMID: 10927053]
  • P Soucy, V Luu-The. Conversion of pregnenolone to DHEA by human 17alpha-hydroxylase/17, 20-lyase (P450c17). Evidence that DHEA is produced from the released intermediate, 17alpha-hydroxypregnenolone. European journal of biochemistry. 2000 Jun; 267(11):3243-7. doi: 10.1046/j.1432-1327.2000.01349.x. [PMID: 10824109]
  • S Marui, M Castro, A C Latronico, L L Elias, I J Arnhold, A C Moreira, B B Mendonca. Mutations in the type II 3beta-hydroxysteroid dehydrogenase (HSD3B2) gene can cause premature pubarche in girls. Clinical endocrinology. 2000 Jan; 52(1):67-75. doi: 10.1046/j.1365-2265.2000.00873.x. [PMID: 10651755]
  • J L Sadoul, B Kézachian, S Altare, Y Hadjali, B Canivet. Apparent activities of 21-hydroxylase, 17alpha-hydroxylase and 17,20-lyase are impaired in adrenal incidentalomas. European journal of endocrinology. 1999 Sep; 141(3):238-45. doi: 10.1530/eje.0.1410238. [PMID: 10474121]
  • M Hill, R Hampl, D Lukác, O Lapcík, V Pouzar, J Sulcová. Elimination of cross-reactivity by addition of an excess of cross-reactant for radioimmunoassay of 17alpha-hydroxypregnenolone. Steroids. 1999 May; 64(5):341-55. doi: 10.1016/s0039-128x(99)00017-3. [PMID: 10406484]
  • M Hill, D Lukác, O Lapcík, J Sulcová, R Hampl, V Pouzar, L Stárka. Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects. Clinical chemistry and laboratory medicine. 1999 Apr; 37(4):439-47. doi: 10.1515/cclm.1999.072. [PMID: 10369116]
  • T Imai, J Tobinaga, T Morita-Matsuyama, T Kikumori, H Sasano, H Seo, H Funahashi. Virilizing adrenocortical adenoma: in vitro steroidogenesis, immunohistochemical studies of steroidogenic enzymes, and gene expression of corticotropin receptor. Surgery. 1999 Apr; 125(4):396-402. doi: 10.1016/s0039-6060(99)70007-3. [PMID: 10216530]
  • J L Ponthier, C H Shackleton, J M Trant. Seasonal changes in the production of two novel and abundant ovarian steroids in the channel catfish (Ictalurus punctatus). General and comparative endocrinology. 1998 Aug; 111(2):141-55. doi: 10.1006/gcen.1998.7096. [PMID: 9679086]